{"title":"Merging Au(I)-Catalysis and Biocatalysis: Practical and Scalable Synthesis of Chiral Amino Building Blocks from Alkynes","authors":"Meriem Daghmoum, Nazarii Sabat, Meije Lecoq, Thelma Viraize, Xavier Guinchard","doi":"10.1021/acscatal.4c07259","DOIUrl":null,"url":null,"abstract":"Au(I)-catalyzed hydration of aliphatic terminal alkynes is followed by transaminase-catalyzed reductive amination, leading to enantioenriched chiral amines. The approach features a one-pot reaction with no particular need for a compartmentalization strategy. Final functionalization performed <i>in situ</i> leads to a variety of chiral amines, pyrroles, and 1-pyrrolines obtained in high enantioselectivities. The method demonstrates applicability to the synthesis of bioactive drugs such as clobenzorex (43% yield, 3 steps, 96% ee) and a precursor of lisdexamfetamine (34% yield, 3 steps, dr 98:2).","PeriodicalId":9,"journal":{"name":"ACS Catalysis ","volume":"38 1","pages":""},"PeriodicalIF":11.3000,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"ACS Catalysis ","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acscatal.4c07259","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}
引用次数: 0
Abstract
Au(I)-catalyzed hydration of aliphatic terminal alkynes is followed by transaminase-catalyzed reductive amination, leading to enantioenriched chiral amines. The approach features a one-pot reaction with no particular need for a compartmentalization strategy. Final functionalization performed in situ leads to a variety of chiral amines, pyrroles, and 1-pyrrolines obtained in high enantioselectivities. The method demonstrates applicability to the synthesis of bioactive drugs such as clobenzorex (43% yield, 3 steps, 96% ee) and a precursor of lisdexamfetamine (34% yield, 3 steps, dr 98:2).
期刊介绍：
ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels.
The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.
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